In candid remarks, the former exec, now on the board of Time, Inc., compares Sony to a cemetery and says he’s not so sure Time will survive in the digital world

In a frequently humorous address to several hundred entertainment lawyers and others, former Sony CEO and chairman Sir Howard Stringer shared observations from a half-century career that ranged from service in Vietnam to leadership of two media giants, offering uncensored thoughts on Sony and Time Inc., the Time Warner print/online spinoff whose board he recently joined.

“At age 72, I’m one of fifty shades of grey trying to stay relevant,” he remarked, evoking laughter across the crowded USC ballroom. He stressed how difficult it is for any individual or company to respond to disruptive innovation, and discussed the threat to the BBC’s survival, on whose board he also sits.

Asked by The Hollywood Reporter to assay the survival prospects of the other media company he helps shepherd, the now standalone Time, Inc., Stringer was blunt.

“It’s a real tricky one,” he said. “I don’t know if we can pull it off.”

He cautioned that he was still new to the board, and was soon to attend just his second meeting.

As to the BBC, Stringer told THR that that company was the one he’d like to lead, were he to take an operating role somewhere.

The executive is best known for his tenure at Sony, and before that at CBS, where he spent thirty years as a writer-producer, director and executive, including as president from 1988-1995. He joined Sony in 1997, became chair and CEO of Sony Corporation of America the following year and was elevated to those same roles at the parent Sony Corporation in 2005.

“My Sony bosses thought I could wake up an analog dinosaur,” said Stringer, referencing the company’s displacement by Apple from its once dominant position in personal electronics. “It was clearly a bridge too far.”

“Steve Jobs … saw the advantage of an open platform,” he observed, while Sony clung to a “not invented here” mentality that Stringer said suited the analog world but not the digital one.

Later in the speech, he returned to the subject of the Japanese electronics maker. “Running a big company is like running a cemetery: there are thousands of people beneath you, but no one is listening.”

Stringer, a Welshman, received a BA and MA at Oxford. “I read history,” he said, “so there was no one at university who thought I was going anywhere.” Eager to leave the stratified society of the UK, and inspired by American movies and by Rhodes Scholars he’d befriended, he sought employment in America. He wrote every TV network, but only CBS responded.

“We don’t give jobs without an interview,” sniffed the Tiffany network’s letter discouragingly. But Stringer saw that as an invitation. He saved up £100 and sailed – yes, sailed – from Southampton to New York, missive in hand.

When he showed up at CBS, the network was so abashed, as Stringer describes it, that they gave him an interview, and then a job answering phones at the Ed Sullivan Show. He rose from there through news and documentary divisions, winning many Emmys along the way, ultimately attaining the top slot.

But his 30 years at CBS weren’t uninterrupted: Early on, he was drafted and served in Vietnam. Noted entertainment attorney Bruce Ramer, who introduced Stringer, explained it thus: Stringer had applied for a green card and was being interviewed by a government employee, who asked him hostilely, “What makes you think you can get a job in the U.S.?” Stringer’s reply – “Well, you did” – didn’t win him any favors, though Stringer says it was his status as a green card applicant, not his cheeky answer, that made the then-U.K. citizen draftable.

There were moments of pathos in Stringer’s address as well. He told of being bullied in school and of how having his tormentor over for tea didn’t end the abuse. (Learning to box and punching him in the face did, however.) He also told of painfully working up the courage to put his hand on a date’s arm at the cinema, only to discover when the lights came up that he had instead been “flirting with a plastic arm” – the arm of the theater seat. He never saw the girl again.

“I remember all my failures as if they happened yesterday,” Stringer confided, bringing surprised and sympathetic murmurs from the audience.